Morning Quickies: “Should I Confess to My Boss that I’m Deeply In Love with Him?”

New Here? Welcome! Dear Wendy is a relationship advice blog. You can read about me here, peruse the archives here and read popular posts here. You can also follow along on Facebook and Instagram. If you have a relationship/dating question I can help answer, you can send me your letters at [email protected] (be sure to read these guidelines first). Thanks for visiting!

The story starts when I was hired for a new job via phone interview. The man that I spoke to was funny, confident, and calm, and immediately I developed a crush. All this without even seeing what he looked like. This crush developed over time to an infatuation and then eventually a deep love, but I’m getting ahead of myself now. Because of the structure of our job, we all work in different cities, connecting through email or phone calls and only seeing each other a handful of times a year. My feelings for this guy (who is technically my boss) grew stronger and stronger as we got to know each other. He is everything I’ve wanted in a man plus so much more; I would feel like the luckiest girl on this planet if I could be with him.

We went a whole year without my confessing my feelings for him, but we grew closer and closer in a friendship with a lot of teasing and possibly flirting. He is so kind and considerate that my heart just melts every time I speak with him. He remembers details of my life and is always asking about specific points that most people would forget. He drove me to the airport, a 30-minute drive away, at 4 a.m. when he had to be there later on in the day to catch his own flight. He opens doors for me and treats me like a lady. This is part of who he is, but I can’t help but take these gestures as a sign that he likes me as well.

Last year I finally worked up the courage to tell him how I feel. (Albeit with liquid courage, but it was better than nothing). His response to me was that it can’t happen and that he was not going to change how he acted around me. I was a little heart-broken but still held hope. Another year and a half has gone by and my feelings are stronger for this beautiful man and I am the most confused I have ever been. It is quite evident that we have a connection and that we get along tremendously. This is not only my silly girl brain saying this — I have colleagues who know about my crush and have said that exact thing.

Logistically, it’s even more confusing. When we first started, we lived within 6 hours of each other but then he moved to the other side of the country. He recently decided to move back home, and now I’m moving to where he was last year. He is coming to see me at the end of the month before I leave, and I need to tell him my feelings. I know I have to do it to get it off my chest. If his feelings are reciprocal, then what an amazing story; if not, at least I can get a hard no and try to move on. I should also mention that there is a possibility that I will no longer be working with this company next month.

My question to you, Dear Wendy, is: Should I tell him, and, if so, how do I do it? — Hoping for an Amazing Story

I’m confused. Didn’t you ALREADY tell this man how you felt about him? And didn’t he ALREADY tell you that a relationship between you can’t happen? Regardless what hints about his feelings for you you think you’ve seen or what other colleagues think they have seen (and they don’t know what is going on in his head any more than you do, unless he’s actually told them), this man/your boss knows that you are into him and, if he wanted a relationship with you, he would have initiated one. Personally, I would leave this alone until, at the very least, you are no longer working under/with him. Maybe he IS into you but doesn’t want to compromise his job by starting a relationship with someone who is technically a subordinate. Or maybe he’s not interested in a long-distance relationship. So, I would wait until the threat of rocking the boat at work has passed (i.e. you no longer work with the man) before you make another play for a relationship with him. Just be prepared to get an answer you don’t want. After all, you’ve already gotten an answer you didn’t want. The likelihood that the answer has changed without you knowing about it is pretty slim.

I have been in a relationship with my fiancé for over two years (I am 27, he is 30), and I have been engaged to and living with him for over a year now. The situation of living together was unpleasant from the very beginning. We met at work, which is three hours away from my home, while he lived at home when we met. Our cultures are VERY different, to say the least. When I moved in with him, we lived at his aunt’s house, which is a minute walk from his parents. We had absolutely nothing, except a bed and toilet — no shower, no closet, no kitchen. It was only temporary though because his parents were repairing a house for us to live in, which we moved into after eight months of living at the aunt’s house.

I’ve always lived away from home (since 19) and seeing his parents every day when we lived at the aunt’s house (for showers and eating all meals), drove me crazy. Now, we’ve been living in “our” house and nothing has really changed; I still have to see his parents every day, and I just hate it. I’ve told my boyfriend that several times, and I even asked him to leave an option open for maybe moving away because I won’t be able to live here for long. And he said that, no, he’s not leaving!!

So he gave me two options. I either accept this situation (and I can’t) or I move. But I really love him. What do I do?? It is driving me crazy. I’ve been very supportive; I’ve lived at his aunt’s house for eight months because he asked me to (money issues), but now I just don’t see the point. We both work. I want to have the same relationship with his parents as he has with mine — seeing them once every two weeks or so. What do I do?? — Tired of Seeing His Parents Every Day

You take the more bearable option. You either accept the situation that your boyfriend says will not change (staying where you are, seeing his parents every day) or you break up and move away. Those are your choices. You may not like them, but not liking something doesn’t change the fact, and the fact is that your boyfriend will not change his relationship with his parents to appease you. If it were I, I’d cut my losses and MOA. There are other men out there who are perfectly happy only seeing their parents every couple of weeks as you want.

I mostly agree with all points made here. Except i think it’s a bit unfair and a bit much for the 2nd LW to break up with the guy. Move out? Absolutely, that’s what i would suggest, but I personally don’t think it’s something he should be broken up with over.

I have to respectfully disagree, 2_J. LW2 and BF have totally divergent opinions of the amount of time to spend with their respective parents. This is not something that is going to magically disappear or one party is just going to decide to go with the flow on. To me, this is a definitive “I love you but we arent compatible” type situation.
*
I also dont understand the commuting part. If you both have jobs and can therefore presumably have a place of your own (or own respective places), why the commute?

I agree–I don’t get why it would be unreasonable to break up. They are engaged. This is behavior he isn’t willing to change. This isn’t behavior she’s willing to put with. So her options are deal with it, which she says she can’t or break up.

How exactly would moving out help? They’re engaged. They’ll have to live together eventually and he already said he wasn’t leaving. They really only do have two options, and Wendy covered those.
.
If you’re suggesting she move out, stay with him and try to wear him down so much so that he leaves…. well then that’s not a good plan either. I have you to force someone to do something or be something, then you are with the wrong person.

This fiancé has been very rigid about what kind of life both him and his wife will have. Maybe it is smart to save money and they do have their own house. But she hates it and is unhappy. That should be enough for the fiancé to take things seriously and be thinking about ways to accommodate them both. Marriage requires compromise and vision. This letter writer could take some innovative to make herself happy by moving out or being busy when mom and pop come around. But having already moved three hours away and being willing to live your relationship around extended family is a lot. It sounds like the effort of coming up with a vision that works for both of them is going to be too hard, here. You can love someone deeply and still not share the same fundamental desires for your joined life.

Wait I’m confused about lw2 – you committed three hours each way to work or that your family lived 3 hours away from where you lived when you met him? If its the latter you should really go back to your old situation since I don’t understand why you moved in with him in the first place if you had to live with his aunt without your own shower…

Sigh. Rejecting others’ reality and substituting your own is only cute on a t-shirt, LW’s.
.
LW1: He’s just not that into you, and by “not that” I mean “not at all.” You don’t say *why* he told you no the first time around, which I find curious, but in the end, it doesn’t really matter. Your boss sounds like a really nice guy who handled what had to be an awkward and uncomfortable situation for him with a lot of respect, compassion and class. Please return the favor and show him the respect of accepting his answer: he doesn’t want to be with you romantically. The end. Stop fixating on him, let this crush go, and find someone who does want to be with you.
.
LW2: You say you and your fiancé are from different cultures. Is his one that values being near family? Again, just curious, because the why doesn’t really matter. He is close to his family and isn’t interested in distancing himself from them. Not even for you. Wendy is right, you have two options: accept it or leave. But, before I leave, I’d think about why I find the family situation so intolerable because *that* might be something you and your fiancé can compromise on. Are they disrespectful to you or your relationship? Do they have no boundaries? Are they around all the time? Are they involved in everything you do? If it’s something like this, then why not work with your fiancé to set some ground rules?
.
Or is it just that you find being that close to his family smothering? Because, I do get that. But maybe instead of considering them “his family”, you can try to look set them as “people” and see if you can find some commonalities as friends. Basically, develop your own relationship with them. After all, if you and your fiancé get married, these people will be your family, too. Might as well get used to the idea.

LW1, Wendy is absolutely right. You told him, you got an answer.
*
We as women need to collectively understand that the rom-com movie endings DONT HAPPEN IN REAL LIFE. “His response to me was that it cant happen… I was a little heart-broken but still held hope.” Please dont hold onto this hope. The maxim “no means no” applies in so many contexts, and most definitely here. It is time to let your heart heal now.

I always liked you, Bon Viv. 🙂
*
When the whole “he’s just not that into you” phenomena blew up like, what? 10 years ago, I didnt like what it became (like over commercialized, I mean)…but the basic concept is spot on. As women, we want to talk through every.damn.thing, and quite often the answer or whatever is RIGHT in front of us. If someone tells you something or shows you something by their actions, take this at face value- man or woman. Trying to read into things or small gestures, etc will just tie you up in knots sometimes. Especially when you are seeking a certain answer and will try to get there any way you can. I know I was guilty of over analyzing stuff with SO many men in my teens and 20s. Looking back…ugh… never mind. Suffice to say I cringe at my past actions.

Yes, yes, yes! I cringe at my past actions as well. For example, in my past I’ve I stayed with a guy who told me 3 months into the relationship “I think I’m still in love with my ex wife”, pined over a guy who would call me to hang out and would tell me he loved me when drunk but that we couldn’t be together, and dated a guy that I didn’t care about that much who would never make time for me. I remember seeing “He’s Just Not That Into You” and crying because it spoke to my experiences. Now that I’m finally with someone wonderful, it couldn’t be more clear how not into me those guys were, and how into me this guy is. I haven’t had to over-analyze a single thing with my boyfriend from the beginning. No “what does this text mean?” or “I haven’t heard from him”. It’s wonderful!

So true. How many times have I heard girls try to explain away why a guy hasn’t been texting them. “Oh he’s super busy”. “I know he’s been stressed at work and going to sleep early”. Girl if he wanted to text you he would. No matter how busy he has a moment to text. He just doesn’t want to.

Ugh yeah, I think we all cringe at some of our past actions like that. The “He’s Just Not That Into You” thing was really a gamechanger, in that it’s so simple and true. I overheard a couple of girls in my work cafeteria discussing one of their issues with a guy, like “well he hasn’t texted me back yet but I know he’s busy with work etc etc” and I really wanted to go up to them like Miranda in SATC and say “I’m sorry, but he’s just not that into you. I’ve just saved you boatloads of time. You’re welcome.” But I didn’t get the impression they would appreciate that…

LW1, you’ve built this whole “story” in your head, but it’s not reality. What you have here is a massive crush on a man you idolize. You see him a few times a year and he treats you like a total gentleman. Ok. Is he in sales by any chance? Because what you describe sounds a lot like the way the sales guys I work with treat me when they’re in town or I travel with them. Minus ANY kind of romantic feeling on either side. They’re kind and considerate. They remember details and ask questions. They always are willing to pick up and drop off at the airport rather than let me take a cab. They open doors and carry things. That’s just how they are, they’re sales guys and they’re gentlemen. I don’t know, I think you’re living in a self-constructed fairy-tale. You’re obsessed with this guy and you see some great future together, but he’s not thinking that way at all. You’ve got to get a grip, realize this isn’t happening, and be dating guys who are available and into you.

This! I was coming here to write almost the exact same thing. It sounds like this guy is a genuinely charismatic, warm individual and you are misreading his kindness as a signal that he has feelings. I have had this happen to me a few times – I am interested in people in general and remember details and show interest in my coworkers’ lives. A few men have misinterpreted my friendliness and thought I was into them romantically. But I was just being nice, and I did like them as people. Just not “that” way. Whatever you do, don’t put him in an awkward position twice. He already told you that he’s not interested and you need to take him at his word.

Totally agree with you Kate. My husband is a salesman and many times when he is on the phone setting up appointments, he will ask clients (who are 98% women) what could be construed as “detail-oriented” things. That is part of his job–to make an interpersonal connection and meld that into the business. I’m sure when he goes to markets, he also holds doors for women too; doesn’t mean he’s wanting a romantic relationship with them. LW has totally built up some fantasy relationship in her head, with every action by him being misconstrued as a sign that he wants her, if only she could convey to him how she REALLY felt…again.

Personally, when I’m rejected, I take it for what it is, which is a no. Then I act or adjust my feelings accordingly. That’s just me though. To each their own.
.
LW1, I think you made up your mind already and are going to say something. You just wanted strangers on the internet to tell you to go for it because, duh, after everything you said, of course he’s harboring deep feelings for you. And they lived happily ever after. (I’m being snarky. I actually think the exact opposite).

Ok, done! (I’m a slow reader.) My substantive answer of “no” still stands but “HELL NO!” is too strong. That’s what I would have said if she had asked before she told him the first time, and the all-caps and exclamation mark and the tone with which I said it in my head all carried with it a warning of the effects “because if you do you’ll lose your job and your dignity and fuck i bet he’s married and so just don’t do it.” But here, she’s already told him, and she didn’t lose her job so likely hasn’t nothing to lose by saying it again except that now we all know that he already knows and hasn’t done anything about it so he’s probably not going to reciprocate when she says it a second time so I’d like to change my answer to a more subdued “no, just let it go.” (Maybe I over thought it. “HELL NO” works fine too, ha.)

Tell you what LW1, since you seemed to have already made up your mind to say something – say it. Just WAIT until you two are no longer working together. That way you won’t disrupt a working relationship and (more importantly you can get a clean break and move on for good.

LW1, noooooooooooooooooooooooooooo. You sound like I did with my crushes in college as I explored dating-ish behaviors for the first time. I look back and cringe at what I did. I feel like you’ll feel the same way about this. And I didn’t even have my work on the line at the time. Don’t do it, spare yourself. He’s already told you how he feels and what he thinks!
*
LW2, you and your fiance should’ve communicated better prior to moving in together. You clearly knew that this was his preference, but you thought that would change. Many cultures prioritize extended family and clearly you emphasizing different cultures makes me think that you prioritize extended family differently.
It’s different for every person. My friend goes back to every weekend to her parents as her brother recently passed. My brother likes to go 1-2x monthly and used to go every week before having 2 kids made it difficult. I like to go 1x or less monthly as I like to be by myself a lot. I wouldn’t have moved into that situation and communicated why.
Your boyfriend sounds like he’s been upfront. Make your choice, learn to live with his parents or MOA.

LW1, what you’re describing is a man with good manners. Not a man who is in love with you.
.
I have a friendly relationship with several of my male coworkers. We tease each other. They hold doors for me, and I’m sure they’d drop me off at the airport if I asked them to. We remember specific details of each other’s lives.
.
This is not being in love. I have no romantic interest in them, they have none in me. This is just how friendly coworkers behave.
.
I’m sorry, but you’ve created a relationship in your mind – one that doesn’t exist in the real world. He’s *told* you that it doesn’t exist. You can’t make people fall in love with you, no matter how hard you try, and no matter how much you want it.
.
It’s good that you’ll be changing jobs. Don’t make some grand romantic confession. You’ve already told him how you feel; he’s already told you that he doesn’t feel the same way. To do it again would just embarrass him and make for an incredibly awkward situation. Just let it go, and move on.

LW1, this is for you, from my own experience. You’ve already told this guy how you feel. It may be that the reason he says it can’t happen is because you work together. Well, if it’s true that you will no longer be working together, I say this you wait until that happens (this is most important) and then you tell him that even though you’ve told him before how you feel and you’ve heard his feelings, if things ever change and he would like to go out somewhere, you’d be open to it. Then you leave the ball in his court and get on with your life. You do not contact him in any way, leave it up to him. If it’s meant to happen, it will. If not, life goes on.

I really like this advice, Kate. I know I was snarky. But I think the best way to handle something like this is wait until they no longer work together, say something like you just mentioned and then do your thing. No pressure. No pining away. At least she’ll be able to say that she did all she could and not have any “what if” regrets.

I agree. But do we know why he said no? Was it because they worked together and now they won’t? Did he have other reasons, like timing? Distance? Or was it truly that he didn’t like her “that way.”
.
I honestly don’t see the harm in revisiting it ONCE. Circumstances change.
.
Personally, I wouldn’t revisit it. Once I’m shot down, that’s it for me. But as I said, to each their own.

FFS LW1 are you 12 and thinking that your boss is from a Twilight movie!?!
.
I feel sorry for LW1, but even worse for the poor boss, hence the harshness. She has spent more than 2 years living a complete fantasy, the first year in which she fell into a “deep love” with someone she apparently saw in person a couple of times. That’s not love, that’s crushing to the point where you have become delusional, and even being firmly and kindly rejected did nothing to disuade her. Take no for an answer, move on and please PLEASE stop watching romantic comedies… you are rapidly approaching the point where you could become a stalker because you aren’t taking people at their word, preferring your dream to reality. All the while you have basically wasted 2 years of your life pining for something unrealistic and unavailable to you… get out of your office and try to meet someone who is interested in you before falling into a “deep love”

Am I the only one who thought him saying he wasn’t going to change how he acts around her was kind of an a*hole move? “I know you think I like you because of the way I behave and though I don’t want to be with you, I’m going to continue behaving this way and leading you on and feeding your fantasy that I like you?” Maybe I’m just cynical, maybe he just meant I’m not going to act weird around you now just because you said that (which would be a very nice answer), but I kind of took it the first way. I know it’s not his responsibility to change the way he acts based on her feelings but, you know, if he’s so nice and knows how she feels but doesn’t reciprocate, maybe he needs to pull back a little, knowing that it’s making it confusing for her.

LW1: Jeez, I act nice to pretty much everyone, take an interest in their lives and remember details to show mutual respect. And I work on the charitable sector, which is about 85% female. I wonder how many of these people think i’m in love with them? Or think they’re in love with me? Maybe I should rethink this whole monogamy thing. In fact, that’s why he told you it can’t happen. Because he has a waiting list a mile long of ladies he treated politely who have fallen in love with him. There are only so many hours in a day.

I’ve definitely had guys think I was interested just because I was being nice. And I don’t have a flirty personality at all. I’m really uncomfortable and not good at it, so I know for a fact I wasn’t flirting with them.
.
I had one guy who I met at another office, across the continent from me. Everything seemed fine when we were working together, I thought we were being colleagues. When I got back home, he instant messaged me through our work system and asked if I wanted to “give this a try”. I’m like, give what a try? I seriously didn’t even know what he was talking about. When he made it clear, it was sooo awkward. And I actually kind of disliked him, so I definitely was not sending signals.

“This is not only my silly girl brain saying this” – don’t lump all of the female gender into your delusions. This is all in your head, and not just because you’re a girl. MOA and do not subject this guy to another painful, awkward confession of your feelings.

I think she can just go ahead and drop “girl” out of the phrase. Then it would be accurate.
.
I really don’t understand people who insult a whole group that they’re part of when they screw up. The first time I ever heard a senior use the phrase “a senior moment”, I was so confused. Are you trying to reinforce the stereotype that seniors aren’t always with it? Same thing with “a blonde moment”. Are you agreeing that blondes are dumb? It’s just so strange to me.

LW1, if you haven’t already seen the movie “He’s just not that into you”, see it, if you have, see it again, you will recognize yourself. Not trying to be mean, we’ve all been there, but this is in your head. If he wanted to be with you he would have made it happen. If your job relationship is the barrier, he will make it happen once you aren’t working together anymore. Keep your mouth shut and see what he does.

LW1 if he wanted to be with you at this point he would. Also how awkward that people in your office know about this crush and discuss how well you get along. Your crush is bordering on the concerning. If you’re older than 16 I think you need to work on getting out of the house and meeting more people. You say yourself that the nice things he does are just who he is, but you still let yourself believe he likes you because of them. Hopefully moving to a new place will create new life experiences and you can move on from this crush.

LW 1: Are you kidding? You must be kidding. For a grown woman who has a full time job to have this obsession with a guy who ALREADY SAID NOTHING WOULD HAPPEN , I hope you would have more self respect than that. It’s not happening. It will never happen. This is NOT love, it’s infatuation and obsession. You are painting this picture in your head and in the process you are cutting yourself off from meeting potential guys who are available to you. Just think, in the past year or so you’ve probably missed a good deal of dating opportunities just because you’re so focused on and obsessed with your boss.

Just because you were drunk when you confessed doesn’t mean his answer wasn’t real. Can you imagine what else you could have found out in this world the last two and a half years if weren’t infatuated with this guy. Talk about a waste of time.

LW2: Shit just ain’t going to work. He clearly doesn’t love you enough to not see his parents everyday, so if I were you I would call it off now.

LW1 – Girl, he told you that he wasn’t interested in a relationship with you but was also kind enough to reassure you that he wouldn’t change how he acts around you (i.e. make things awkward since he expressed feelings and they were unrequited). And then in the last year and a half, all while you think you are getting all these sign and signals, he still hasn’t made any attempt to have a relationship with you or even share any feelings other than friendly coworker. Get over it. He’s not into you.

This really resonates with me. I was recently “allowed to resign” from a career type job for being on the receiving end of LW1’s kind of crush.

A young lady that I worked with decided that since I was kind, polite and asked about details of her life (no differently than I did my other co-workers, both male and female) that I must have romantic feelings toward her. She evidently “developed feelings” as she made a liquid fueled confession at an office function. I reminded her politely that I was not interested, that I am married, and that my wife was in attendance at the event!

Two weeks later, I was called into HR, suspended, and, after consultation with the corporation’s legal counsel, left the organization, because she had complained about my behavior toward her and that she no longer felt comfortable working with me. The organization had no interest in defending me, partially because I was leaving anyway and had just given them 3 months notice.

Tread lightly! The ripples of our actions have consequences we do not intend!

Oh, they knew it was unfair. So they gave me the 3 months of salary until my planned departure date, and we parted on good terms. They decided that it was easier to do that than fight either side of the battle.

She was terminated about 6 weeks later. She basically stopped showing up to work!